Why didn't you do it?

I left Belgium for San Francisco, and the move reset how old I was allowed to be.

In Belgium, where I'm from, you're not taken seriously until you're 30. In San Francisco, by 30, you're already a little old. I'd moved from a country that thought I was too young to one that thought I was slightly past it. There's real power in accepting that the choices you make now are the ones you'll answer for later.

I don't mean that as a threat. I mean it as permission.

The question

Here's a question I don't think we ask ourselves nearly enough. Say you died tomorrow. Nothing dramatic, no story to it, just gone. What would you be sad you never got to do?

It sounds morbid. It isn't. It's the fastest way I know to find out what you actually care about, because it burns off everything you were only doing to look busy and leaves the few things you'd genuinely grieve. Most of the noise doesn't survive the question. Whatever does is worth looking at properly.

We avoid asking it because it's uncomfortable, and because as long as you never ask, every path stays open in theory. The moment you answer it honestly, a few doors close and a few others start to matter enormously. That isn't a loss. That's just finding out where you actually stand.

The two questions

When I talk to people my own age in Europe, the difference in mentality is substantial, and it's the thing I keep coming back to.

I end up asking the same two things every time. What's your long-term goal. And how does the job you're in now, or the decision you're about to make, actually get you closer to it.

Most people go quiet. Not because they've got no answer, but because they've never had to say it out loud, and the question lands like an accusation. It isn't one. It's a map check. You're allowed to stop, look at where you're standing, and ask whether this road actually goes where you once said you wanted to go.

Part of it is that Europe is very good at offering a safe path, and a safe path is a genuinely nice thing to be handed. There's a sensible sequence, and if you follow it, nobody will ever be able to say you did anything wrong. The trouble with a route built so you can't be blamed is that it's optimised for not being blamed, which is not the same thing as the life you actually wanted. You can do everything right by that standard and still end up somewhere you never chose.

So the question spooks people. Someone will be halfway through explaining a promotion, or a move, or a course they're thinking of signing up for, and you ask how it connects to where they actually want to end up, and the whole thing stalls. The honest answer is often that it doesn't connect to anything in particular. It's just the next available step. And the next available step is not a plan. It's drift with good posture.

Phases

The uncomfortable thing underneath all of this is that life runs in phases, and the phases don't wait for you to feel ready.

The window for the kind of progression that compounds, the moves that set up the next 10 years, is a lot narrower than it looks from inside it. There's a stretch where you can take a real risk because you've got almost nothing to lose. Then there's a stretch where there's a mortgage, or a kid, or a title you don't want to hand back, and the exact same risk costs 10 times as much. The window never announces that it's closing. It just gets more expensive to do the thing, a little at a time, until one day the thing is something you talk about at dinner instead of something you do.

Belgium and San Francisco just draw those lines in different places. One tells you you're too young to matter until 30. The other tells you you're already late by 30. Both are partly wrong. Both are load-bearing anyway, because the story a place tells you about your own timeline changes what you'll let yourself attempt inside it. I felt more permission to move fast the week I landed than I had in years, and nothing about me had changed except the map I was standing on.

Luck

So here's the fundamental thing, and it isn't clever. Don't leave it up to luck.

Luck is real, and it's a bigger factor in all of this than any of us likes to admit. Plenty of what happens to you was never yours to control. But leaving it up to luck is itself a decision. It's just the one you make by not making one. You can't control the roll. You can control whether you turned up to the table with a plan or a shrug, and over enough rolls that difference is most of the game.

The people I know who look lucky, up close, mostly aren't. They decided what they were aiming at early, and then kept putting themselves in the rooms where the good kind of luck was even possible.

The plan

Making the plan is the boring part, which is exactly why people skip it.

Find out what you actually find important. Not what you're supposed to find important, not the version that sounds good said out loud to other people. Then find out how you want to be remembered, and be specific about it. Not the job title. You, as a person. Your values. What you did for the people around you. The mark you left on the world, however small it turns out to be.

Then take that whole picture, the person you're trying to have been, and make it the thing that drives the decisions. Not the salary on its own. Not the logo on the badge. Not what your peer group will make of it at the next dinner. The real question is who you're trying to become, and once that's fixed, most of the things you were agonising over turn out to be negotiable around it.

I should be honest that I'm not writing this from the far side of it. I forget it constantly. The grind is very good at dressing the next available step up as a strategy, and I've taken plenty of steps that were really just motion. Motion feels like progress right up until you look up and notice you've been busy in a direction you never chose. The plan almost never fails because it was wrong. It fails because you stopped looking at it.

Where I landed

None of this is special and none of it is new. Every generation hears some version of it from someone slightly older who wishes they'd listened sooner, and I'm aware I've become that person now, saying a thing that's halfway to a cliché.

But a cliché is just a true thing that got tired from being repeated, and this one is true. In the grind, we all forget it. So I'll leave you with the version that still makes me move, the question I try to picture being asked right at the end, about every risk I talked myself out of and every plan I never sat down to make.

Why didn't you do it?